The Chicago White Sox were one of the most disappointing teams in the American League last year, failing to make the playoffs after winning the American League Central Division a year earlier. They hope to have a stronger team on the field in 2023, and adding outfielder Andrew Benintendi may help them achieve that goal.

Benintendi, who was traded from the Kansas City Royals to the New York Yankees at the trade deadline last year, agreed to a 5-year, $75 million deal Friday with the White Sox, according to MLB insider Jeff Passan.

Benintendi has become a well-traveled player, as the White Sox will be his fourth major league team. He started his career with the Boston Red Sox, and he enjoyed his greatest success with that team.

Benintendi's best season

Benintendi played 5 seasons with the Red Sox from 2016 through 2020, and he was an integral part of the 2018 World Series championship team. He  slashed .290/.366/.465 that season while hitting 16 home runs, driving in 87 runs and stealing 21 bases.

In addition to his offensive contribution, he has been an excellent defensive player in the outfield. His most memorable play was a diving catch in left field in the 2018 American League Championship Series against the Houston Astros. He robbed Alex Bregman of what would have been a game-winning hit in Game 4 of the series. The Red Sox won that game by an 8-6 score and went up 3-1 in the series. They would clinch the AL title in the following game.

Benintendi appeared to be on the path to stardom during the 2017 season, his first full year in the big leagues. He belted 20 home runs, drove in 90 runs and stole 20 bases while .271/.352/.424. However, he has not topped 20 home runs since.

Benintendi had a respectable 2019 season with the Red Sox that included 13 home runs and 68 RBI, but the Covid-shortened 2020 season was nightmarish. Benintendi played just 14 games that season and hit just .103 with just 4 hits in 39 at bats.

The Red Sox traded him to the Royals in the offseason, and he rebounded quite nicely. In addition to slashing .276/.324/.442 , he hit 17 home runs and 73 runs.

He continued his success in 2022, making the American League All-Star team for the first time in his career. The outfielder slashed .304/.373/.399 for the Royals and Yankees, but he hit just 5 home runs and drove in 51 runs. He had 8 stolen bases, and he may no longer be a threat in that area.

Grade for Benintendi signing: B-

It should be noted that the $75 million deal is the most expensive signing the White Sox have made in team history. The contract is pricier than the $73 million given to catcher Yasmani Grandal in a 2020 four-year deal.

The White Sox lost 1st baseman Jose Abreu to the Houston Astros in free agency, and they are expected to move Andrew Vaughn to that position. That will allow Benintendi to step into the left field spot, where he can employ his gold glove skills.

Benintendi is a solid professional who has enjoyed success on the biggest stages. However, there are questions about his run-production ability.

While he does make solid contact, he does not appear to be a power or stolen base threat at this point in his career.

Still, Andrew Benintendi will be a major improvement on the defensive side, and he has shown the ability to get on base.